


Tangled

by kittenofdoomage



Category: Supernatural
Genre: Anal Sex, Double Penetration, F/M, Fingering, Foursome, Multi, Oral, PWP, Triple Penetration, Vaginal Sex, grace!kink, probably a lot of fucking bodily fluids, straight up porn
Language: English
Status: Completed
Published: 2017-09-19
Updated: 2017-09-19
Packaged: 2018-12-31 17:37:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,935
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12137643
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: PWP with Team Free Will and the reader.





	Tangled

When you were six, you’d dreamed of owning a pony. Not just any pony, but  _ that _ pony; the little chestnut pony that every Barbie doll had, that every other little girl yearned for.

When you were sixteen, you wanted the quarterback of your high school football team to sweep you off your feet, and drive off into the sunset with you; the romantic illicit affair every high school girl desired. The school quarterback had ended up dismembered in the library after your entire town was destroyed, leading you into a world of darkness you’d never expected.

At twenty-six, there was only one thing that preoccupied your thoughts, aside from weekly world saving. Well, three things. All of them tall, dark and handsome. Damaged, granted, but who the fuck wasn’t? And these men were heroes. One of them was an angel.

Not one of them would look in your direction.

Until… they did.

Alcohol had played a major part in the first incident. Dean was first, seducing you with shots of tequila after a hunt that went  _ really _ well, the ones where no one died for a change. God, he’d been a master with his tongue, gentle in so many ways you didn’t expect from him, and you’d woken up with a smile on your face that you couldn’t shake for days. And it wasn’t the only night you spent with the eldest Winchester.

Sam had grown jealous, cornering you one evening when you were alone in the bunker. With an admission that nothing between you and Dean was exclusive, Sam couldn’t hold himself back, and where Dean was gentle… fuck, Sam was rough. He was all edges and muscle, packed in with the biggest cock you’d ever laid eyes on, and the morning after, you’d been walking funny.

Dean had a little smirk on his face that implied he knew exactly why you were wincing when you sat down.

The angel, on the other hand, had been a little less suave about his approach. He watched, constantly, sometimes to the point of annoying you, and it was clear he’d been picking up moves from Dean and maybe from television as he tried to seduce you.

In the end, you grew impatient, and showed him what he wanted, riding him in the library with him still wearing his trenchcoat, and you completely nude.

And that was how it went for a while. You’d sleep in whatever room you felt like, and none of the men argued with each other. When one of them kissed you in front of the others, you blushed, but they showed no outward emotion. It was your show. Until it wasn’t.

There hadn’t been a hunt in a week, and you were itchy for action. Sitting in the library, scouring the internet for anything remotely weird, you didn’t notice Castiel at first. Not until his fingers were on your forehead, and the room spun before you realized he’d moved you into your room. You opened your mouth, ready to ask him what the hell he was doing - you never had any of them in your room - but before you could voice your irritation, you noticed that Dean and Sam were there too.

All three of them were only in their boxer shorts.

“We’ve been talkin’,” Dean drawled, reclining backwards on your bed. “And while we love sharing you around, sweetheart, we’d like to have a little more fun.”

You swallowed, eyeing him nervously. “Fun?”

“I think she is confused,” Cas murmured, looking you up and down. “She didn’t realize that we’d been talking about our… liaisons.” A lump had formed in your throat, which seemed to stop you from speaking as the angel smiled at you, and clicked his fingers. The cold air assaulted your bare skin, and you yelped, rushing to cover yourself.

“Talk about shutting the barn door when the horse has bolted,” Dean chuckled, sitting upright and climbing off of your bed. “We’ve all seen you naked, Y/N. And trust me when I say, none of us have  _ any _ complaints.”

“What are you planning?” you asked, even though you thought you knew the answer.

“We’re going to fuck you,” the elder Winchester said, smirking as he pressed up against you, his cock already tenting his boxer shorts. “All three of us. Wherever, however we want. You’re ours for the night, princess.” It felt incredibly hot in your room all of a sudden, and there was little to no moisture in your mouth. Dean’s eyes were dark as he brought one hand up to tease your hard nipple, and you gasped at the sensation. “You good with that?”

This was your moment to back out, but that sounded like a really stupid idea. Who the hell wouldn’t want to be touched by these three? They were all gorgeous specimens of the male form, even if one of them was a celestial being in a vessel.

“I’m good,” you exhaled, feeling your heart thump in your chest, nodding slightly.

Sam clapped his hands together, making you jump a little, and Dean chuckled, keeping his eyes on yours as Sam got up off of the bed. You tried to follow his movements, but then Dean was kissing you, stealing all of your attention, and when Sam pressed up behind you, pressing his lips to your neck, you were fairly certain you were dreaming the entire thing.

“On the bed, sweetheart,” Dean muttered, his hot breath fanning over your lips as he pulled away. You put one foot forward, ready to move, before Sam had you hoisted up in his arms, and you squeaked in a very unladylike manner. “Castiel, you wanna -?”

The angel was there before Dean could finish his sentence, and as your back hit the mattress, an unseen force pinned your wrists at the level of your eye. Your ankles were held down in a similar fashion, and you whined a little at Castiel’s use of grace. Sam and Dean grinned at you like predators, and a shudder ran down your spine, ending in a pool of heat that filled your belly.

“Well, that’s a nice view,” the elder brother commented, and Sam nodded in agreement, reaching out to trail his fingertips down your face, not stopping even as you sucked in a breath when he gently brushed over your breasts. 

Dean was on your other side, watching as his brother dipped his fingers lower, until you whimpered at the feel of the calloused pads on your mound. When Sam’s fingers slid through your folds, you wiggled impatiently, only for Cas’ grace to tighten around your limbs, and Dean knelt on the bed, leaning over you to block your view of Sam.

“Behave, sweetheart. I know you like bossing Cas around, but we’re in charge now.” The husky timber of his voice, combined with Sam’s fingers on your cunt was enough to have your body tensing, and Dean lowered his mouth to your right breast, trailing his tongue around the hardened peak. He hummed in appreciation, and you kept your eyes glued to his movements, still not quite able to process what was happening.

Sam mumbled something, and Cas chuckled. A second later, your legs were tugged wider, exposing you to Sam’s long, thick fingers, and you cried out when he pushed one into you. “Fuck, she’s wet,” he hissed, and your walls tightened around his single digit, greedily demanding more. “Oh, baby, we haven’t even started.”

The angel’s grace tugged your legs again, pushing them up so your knees bent, allowing Sam even more access. You felt the bed dip, but you could see vaguely see Sam, even when Dean switched to your left breast, tonguing and teasing your nipples. Hot breath made your pussy twitch, and you waited, anticipating a tongue on your slit, but Sam’s fingers were still there, and the heated feeling moved further south.

An unintelligible groan left your lips when Cas’ hot tongue pressed against your ass. There was no doubt as to his intention, and the feeling of his mouth there, with Sam’s touch on your pussy, and Dean’s tongue doing sinful things to your breasts - fuck, you weren’t sure you could even handle all three of them now.

Sam added another finger, keeping a steady, gentle rhythm as you panted and thrashed against the invisible bindings. Cas was tonguing your ass, opening you up, relaxing you. Dean pulled back, before crashing his lips against yours, and the second Sam’s thumb grazed your clit, you screamed, letting the older Winchester swallow down your cries.

You were panting when he pulled away, flushed and needy, but Cas wasn’t interested in stopping. Sam pulled his hand back, angling himself on the bed so he could lick your pussy while Cas tongue-fucked your ass, and Dean stripped his boxers off, kneeling by your head. It didn’t even need a spoken command: you opened your mouth obediently, no hesitation stopping your movements as Dean slid his length between your lips. You sucked and licked at him, timing your movements unconsciously with Sam and Castiel, and Dean groaned at the sensation.

Cas’ tongue disappeared for a second, only to be replaced by the warmth of his grace, identical to the feel of it around your ankles and wrists. “You want this?” Castiel asked, his words vibrating against your thigh. Sam paused in what he was doing, leaning over a little more to watch as the angel teased your ass open; Dean pulled away from your mouth to see what his friend was up to. You couldn’t help but nod, unable to gather enough wits about you to answer with words.

“Fuck, that looks so hot,” Sam whispered, watching as Cas eased his grace into you. “Damn, Dean, you gotta look at this.” They were staring now, watching Cas fuck your ass with his grace. It wasn’t painful, more overly pleasurable, and you were mewling needily.

Dean moaned, stroking his cock, still slick with your saliva, and you realized that you were essentially a porn show for a moment, tied down to the bed with your knees up, the angel’s grace fucking into you slowly and purposefully. “Do you actually get anything out of that, Cas?” Dean asked, keeping his voice low.

Castiel nodded, moving back a little more. “I can feel her. Hot and warm and tight…” he trailed off, palming his cock through his boxer shorts. “Would you like me to give her more?”

Sam nodded, unable to tear his eyes away from you. “I think she wants more,” he replied, and the angel obliged. You felt a second teasing tendril of grace at your pussy, pushing into you slowly, almost mimicking the length and thickness of Cas’ dick, and all at once you felt full to the brim. The grace in your ass swelled, opening you up more, and both brothers were touching themselves at the sight of you strung out on the bed.

“Make her cum, Cas,” Dean growled, stroking his cock harder. “Bet she’ll scream.”

“I can stop that, if you wish,” the angel offered, but Dean shook his head. “Oh. Yes, I like hearing her scream too.”

You were drifting closer, trying to fuck yourself down onto the energy pulsing inside you, but you couldn’t move properly with Castiel holding you. Sam had pulled his boxers off, tossing them aside as he mimicked his brother’s movements.

“She’s close,” Cas growled, and you whimpered, proving him right. He fucked you harder, and you fell into oblivion, clenching tightly around both tendrils of grace, the pressure making you squirt a little. The angel withdrew, releasing you from his hold, and you collapsed, panting and sweating in your completion.

“That might have been the hottest thing I’ve ever seen,” Dean said, his words a little awestruck. Sam chuckled, glancing over at him. “Do you think she can take any more?”

“I can,” you rasped, pushing yourself up a little on your arms. “I want…” A groan split your words and the blood rushed back to your head. “Want all three of you.”

Sam moved a little closer, leaning over you to cup your face. “Where do you want us, sweetheart?” 

You smirked, arching up towards him, trying to capture a kiss from him, but he was just out of reach. “You choose.”

Dean clapped Cas on the back, gesturing to you. “I think you earned first pick,” he instructed, and the angel looked at him in bewilderment. “Don’t be shy, man. You just fucked her with celestial powers; I don’t think she’s got a problem with you doing it with your cock.”

You cried out as Sam touched your swollen, throbbing pussy, smiling as your juices coated his fingers. “She’s drenched.”

“I like her on top,” Cas said, his voice slightly thicker than usual. “I like watching her breasts bounce when she sits on me.” He looked at Dean, who nodded his acquiescence, and Sam withdrew, allowing the angel some space. “Can you sit up for me?” Cas asked, and you nodded, taking his hand for support, and he helped you to get onto your knees, before laying down on the bed next to you. It didn’t take any prompting for you to straddle his lap, grinding yourself down against his tented boxer shorts.

“Er, Cas?” you whispered, plucking at the material separating you from him. “Wanna do something about these?” He arched an eyebrow, looking down, before giving you a coy little smile and the boxers were gone. His heated flesh was a slight shock against your sensitive cunt, and you made a funny noise when he twitched. “Can I -?”

He was one step ahead, pressing at your hips so you’d lift off of him, and he lined himself up, before surrendering control to you. With pleasure, you sank down onto his thick length, moaning wantonly as he filled you up. 

“You want her ass?” Dean asked Sam, who shook his head, smiling. 

“Nah. Wanna come down that pretty little throat,” the younger brother insisted, and Dean couldn’t help but grin at that. Sam had a fetish for throat-fucking, and you’d been one of the only girls able to take the entirety of his twelve inch, thick cock down her throat. “You can have her ass.”

You were too busy grinding your hips down onto Cas, your head thrown back as you rode him, to hear the Winchesters’ exchange. Sam’s hand landed on your shoulder, distracting you, and you turned, looking up at him with wide eyes, pupils pinpointed from arousal. He was holding his dick in one hand, smirking, and you smiled back, knowing exactly what he wanted.

“You okay there?” Dean asked, climbing onto the bed behind you. Castiel automatically spread his legs, allowing the other man access, and it stretched you open even further by default, leaving you gasping as the sensations became all the more intense. 

“G-good,” you panted, struggling to speak as Cas’ cock slammed into your g-spot. “Need more.”

“Oh, I got more for you,” he replied, kissing along your neck. There was the telltale click of a bottle lid, and when his fingers touched against your already tender ass, you flinched at the cold gel on them. “Relax, baby. You know we wouldn’t hurt you.”

“But I like it,” you mewled, making him groan against your shoulder. Reaching up with one hand, you fixed a coy look on Sam, before sliding your fingers around his cock. You stroked him a few times, watching his face, smiling at him. “Wanna choke on your cock, Sammy,” you purred, and he groaned, fisting his hand in your hair and pressing in closer, allowing you to slide your lips down his length.

It was an overload of sensation that made you dizzy, and you wondered how you were still upright when Dean’s cock pressed into your asshole, opening you up easily, probably from the prep Castiel had already given you. You could literally feel their dicks sliding against each other through the thin tissue of your body, and it felt magnificent, especially combined with Sam’s cock easing into place, making your throat bulge with the size of him.

Your moans were muffled as you rode out your second orgasm, using one hand to balance yourself against Sam, whose fingers were twisted in your hair, holding you against him as he fucked harder between your lips. The taste of him was coating your tongue, and your eyes were watering, and when Castiel suddenly bucked up, his orgasm taking him by surprise, you cried out. Your body tightened and Dean grunted, following the angel over the precipice, filling your ass with cum.

You were sobbing now, and when Sam finally finished, grunting his climax, which you swallowed eagerly, you thought you might not be dreaming; you were half convinced you’d died. Dean moved away from you gently, and Sam caught you before you fell, cum dribbling from all three of your used holes. Castiel frowned, watching as the large man cradled you in his arms.

“Was it too much for her?” he asked, and Sam chuckled, nodding down at the smile on your face as you stared up at him. 

“She’s cum-drunk,” Dean laughed, cleaning himself up with his boxer shorts. “Maybe she’s had enough of us for one night,” he pointed out, and you whined, shaking your head a little. “No? Princess, you’re almost unconscious.”

“I just need a nap,” you replied, stretching and snuggling into Sam’s arms. “I wanna play some more.” Sam looked up at his big brother, who shrugged, and Castiel grinned.

“I would like to propose some ideas…”


End file.
